Lead Like a Leader

Personal Leadership Mastery

Blog Post #3 — Find Your Cool Series

Title: The True Cost of Living Someone Else’s Life

You can climb the ladder of success and still feel like a stranger in your own story.

We’ve seen it firsthand — executives with seven-figure salaries, recognition, global roles — and yet a sinking feeling they can’t explain. They’ve played by the rules. They’ve done what they were “supposed” to do. But deep down, there’s a quiet ache: This isn’t mine.

In our innovation leadership work, we constantly asked teams, “Whose need are you solving for?”
When we mapped customers’ journeys or redesigned care pathways, the mistake most systems made was building solutions for the process, not the person.

The same happens in life.

You build your schedule to meet expectations.
You define success by your LinkedIn headline.
You pursue goals that were handed to you, not chosen by you.

And then you wake up one day exhausted — not from the climb, but from chasing a summit that was never meant for you.

That’s the true cost of living someone else’s life.


What It Looked Like in Real Life

I remember leading a corporate turnaround where, from the outside, everything looked like a textbook success. Revenue was climbing. Strategy was sharp. But during a workshop, one of the directors quietly admitted: “I don’t know why I’m doing this anymore.”

We’d all been there. We were experts at delivering business results. But somewhere along the way, we had stopped delivering meaning to ourselves.

That moment became a turning point — not just in the business, but in how we led from then on.

It reminded us of a truth we now build into all our coaching and innovation work:

You can’t build a meaningful life from someone else’s blueprint.


Cool Exercise: Two Lists

Grab a blank page. Draw a line down the middle.

On the left side, write:
“Things I’m doing because I should

On the right side, write:
“Things I want to do”

Now — no judgment. Just notice.

Circle one thing on the want list that’s been ignored.
Cross out one should that no longer serves you.

And then act. Not dramatically — just deliberately.

Because cool doesn’t come from rebellion. It comes from realignment.


Innovation Insight: Stop Solving for Approval

In every transformation initiative, we started by clarifying the end-user’s true need.
Not what the system wanted them to care about. What actually mattered to them.

You need to do the same with your life.
Stop solving for applause. Start solving for alignment.

Ask:

  • What does my future self actually care about?
  • What parts of my story feel heavy — not because they’re hard, but because they’re not mine?

That’s how you begin to reclaim your cool.


Quote to Reflect On

“Be yourself; everyone else is already taken.” — Oscar Wilde


Final Thought

You didn’t come here to check boxes. You came here to build a life that feels right in your bones — not just looks good on your résumé.

It takes courage to release the expectations of others. But the real risk isn’t failing to meet someone else’s vision — it’s never meeting your own.

This is your blueprint now.
Let’s build it.

Leave a comment

About

Embark on an extraordinary journey with John Dempsey and Tom Reynolds at “Lead Like a Leader,” where 80 years of collective wisdom meets a passion for Self-Discovery in Leadership. Dive into our blog, where we unravel the secrets of success from the corridors of one of the world’s largest healthcare companies to the dynamic world of start-ups. Join us in reimagining personal leadership and well-being, as we blend timeless insights with cutting-edge strategies. This is not just a blog; it’s a beacon of empowerment, a sanctuary for truth-seekers, and a roadmap to your fullest potential. Welcome to the straight-talking zone, where learning and sharing never stop.